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In 1969, Robert Matherson bought what was then a waterfront barrier island restaurant and converted it into an enormously popular (and controversial) nightclub. He later opened four more OBI night clubs and named them according to their geographic location. The OBI North was in Smithtown, New York, the OBI East near the Shinnecock Canal en route to The Hamptons and two OBI West locations in Island Park, New York. All five clubs were located on Long Island and were wildly successful for many years, bringing people in from all over Long Island, New York City, Westchester, southern Connecticut and New Jersey. One of the OBI West locations burned down after only a couple of years of packing in thousands on the weekends. Arson involving organized crime figures referred to in the movie "Goodfellas" was alleged but never substantiated.

Over the years, the OBI was involved in many disputes with the local community over issues such as noise, parking and traffic.[1] Finally, in 1999, Matherson sold the property and moved to Key West, Florida to open a new club of the same name. The original property was torn down in 2003.

Robert "Rosebud" Butt is credited with inventing the Long Island Iced Tea while working as a bartender at the OBI in the 1970s.

In 2010 the Babylon based rock band "Two Cent Sam" released the "OBI Song" and a DIY video celebrating the Oak Beach Inn's history and impact on Long Islanders and the void in Long Island night life after the "OBI's" destruction [2]